Date Outside Of Your Generation

They say age is just a number, but does this adage still ring true when it comes to love? If you’re tempted to date outside your generation, we’ve got a few tips for you.

By Bob Strauss

f there’s one thing that characterizes baby boomers — the generation born between 1946 and 1964 — it’s the belief that they can have it all. Regular doses of antioxidants will keep their cells glowing, healthy and disease-free (some of these folks are so saturated with Acai berry products that they conceivably could survive a nuclear detonation). Their retirement accounts will revive as though awakening from a long winter’s nap, shake off the
The answer is as easy as X, Y and Z.
dust with aplomb, and yield 10 percent annual returns for the indefinite future. And, of course, single boomers can date freely amongst the younger generations, regardless of the pop-cultural disconnect that may exist between them.

Who are these younger generations, you may ask? The answer is as easy as X, Y and Z. In broad, completely unfair terms, Generation X (born between 1966 and 1976) is commonly characterized by apathy, cynicism and general disengagement from social issues; Generation Y (born between 1977 and 1994) oozes technological sophistication, an almost slavish addiction to fads and (until recently) easy access to credit; and Generation Z? Well, we’ll have to wait to see how that group turns out; you shouldn’t really think about dating them yet since the oldest members are still under the age of 18.

(Okay, before you send me hate mail, yes, there are exceptions. Some Gen-Xers are married, earnest and optimistic, and it’s statistically likely that at least some Gen-Yers, also known as Millenials, have never used Twitter or listened to 50 Cent. And I sometimes imagine that the bad seeds of Generation Z prowl Internet chat rooms pretending to be bald, 47-year-old men, though that’s a matter for the courts to decide, not me.)

So what should you be aware of when pursuing prospects from different generations? Here are five helpful tips.

1. Pay more attention to your psychological — not physical — age.
Jeannine Kaiser, author of Cupid’s Playbook, offers a wealth of intergenerational dating anecdotes: “Linda, a 56-year-old graphic designer, was full of energy and loved to water ski, play tennis and parasail. She couldn’t find a man in her age group who could keep up with her active lifestyle, so she went to a cougar singles event and met Jack, 16 years her junior, who owned a boat and was a skydiver. They had an instant connection and are now engaged.”

2. However, don’t overestimate your ability to keep up.
Kaiser offers another story, this time with a not-so-happy ending: “Russ, a 53-year-old sales executive, was attracted to women in their mid-20s. He met Heather, who was fun, beautiful and a bundle of energy. She made Russ feel like a young man again. Heather took
Keep your expectations realistic and your mind open.
Russ out to clubs with her friends and they danced all night. Soon, Russ was exhausted and ached for a quiet night at home. Heather announced that it wasn’t fun staying at home with him and ended the relationship.”

3. Avoid falling into traditional parent-child roles.
It’s a scientific (if somewhat icky) fact that baby boomers are also technically the biological parents of Generation Y, which adds an extra wrinkle to the whole dating scene. Kaiser observes one such pairing: “Jane was a successful, 53-year-old executive and a mother to two adult children. When she met Justin, who was in his early 30s, there was instant chemistry and they had a torrid affair. As the relationship developed, it became clear that Justin was a typical 30-year-old and had a bit of growing up to do. When Jane found herself scolding Justin like she would have scolded her teenage children, she realized that the age disparity was problematic and ended the relationship.”

4. Think hard about what you really want.
Most boomers will deny it, but dating someone a generation (or more) younger is usually a transparent gambit to recapture some lost sense of youth. “The reasons people choose a May-December romance are more important than the age difference itself,” says Kaiser. “A person shouldn’t choose a younger partner just to roll back the clock. If a couple is going to develop a healthy, long-term relationship, they need to consider the love they share for each other, their commonality of interests, their life goals and their ability to communicate.” Kaiser adds, logically, that “a 10-year age difference is much more appropriate than a 20-year difference when you consider the health and energy of your partner in the years to come.”

5. Remember, young people think differently than you do.
I’ll admit it: when I was 40 years old, I briefly dated a woman who was exactly half my age. I enjoyed her intellect, her youth, and her athletic body, and she... well, I’m not quite sure what she saw in me. I quickly realized that while I was genuinely dating her in order to build towards the two of us having a relationship, she was semi-seriously exploring what it meant to “date” and have a “relationship.” (The ironic distance couldn’t have been greater if she’d actually used her hands to make air quotes when she pronounced those words herself.) Soon enough, she decided to “date” and have a “relationship” with someone else; who knows, maybe she’s even “married” now.

Bottom line: When dating someone who’s a generation (or two) younger than you, keep your expectations realistic and your mind open. It’s not how old you are, it’s what you see in each other than truly matters!

Bob Strauss is a freelance writer and children’s book author who lives in New York City. He’s also written the Dinosaur guide on, the online information network owned by the New York Times.
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